Catalytic enantioselective cyclopropanation of allylic alcohols using recyclable fluorous disulfonamide ligand

被引:11
|
作者
Miura, Tsuyoshi [1 ]
Itoh, Keisuke [1 ]
Yasaku, Yumi [1 ]
Koyata, Naka [1 ]
Murakami, Yasuoki [1 ]
Imai, Nobuyuki [1 ]
机构
[1] Chiba Inst Sci, Fac Pharmaceut Sci, Chiba 2880025, Japan
基金
日本学术振兴会;
关键词
D O I
10.1016/j.tetlet.2008.07.125
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyclopropanation of allylic alcohols with Et(2)Zn and CH(2)I(2) in the presence of a catalytic amount of fluorous disulfonamide 3 afforded the corresponding cyclopropylmethanols in 69-96% yield with 49-83% ee. The fluorous ligand 3 was readily recovered from the reaction mixture by the fluorous solid-phase extraction (FSPE) and could be reused without a significant loss of the catalytic activity and enantioselectivity. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5813 / 5815
页数:3
相关论文
共 50 条
  • [1] Chiral recyclable fluorous disulfonamide ligand for catalytic enantioselective cyclopropanation of allylic alcohols
    Kawashima, Yuya
    Ezawa, Tetsuya
    Yamamura, Mai
    Harada, Taisuke
    Noguchi, Takuya
    Miura, Tsuyoshi
    Imai, Nobuyuki
    TETRAHEDRON, 2015, 71 (45) : 8585 - 8592
  • [2] ENANTIOSELECTIVE CYCLOPROPANATION OF ALLYLIC ALCOHOLS CATALYZED BY A CHIRAL DISULFONAMIDE-ALUMINUM COMPLEX
    IMAI, N
    TAKAHASHI, H
    KOBAYASHI, S
    CHEMISTRY LETTERS, 1994, (01) : 177 - 180
  • [3] A CATALYTIC ENANTIOSELECTIVE REACTION USING A C2-SYMMETRICAL DISULFONAMIDE AS A CHIRAL LIGAND - CYCLOPROPANATION OF ALLYLIC ALCOHOLS BY THE ET2ZN-CH2I2-DISULFONAMIDE SYSTEM
    TAKAHASHI, H
    YOSHIOKA, M
    OHNO, M
    KOBAYASHI, S
    TETRAHEDRON LETTERS, 1992, 33 (18) : 2575 - 2578
  • [4] Catalytic, enantioselective cyclopropanation of allylic alcohols: Preparative and mechanistic aspects
    Denmark, SE
    OConnor, SP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 36 - ORGN
  • [5] Catalytic, enantioselective cyclopropanation of allylic alcohols. Substrate generality
    Denmark, SE
    OConnor, SP
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (03): : 584 - 594
  • [6] A CATALYTIC ENANTIOSELECTIVE REACTION USING A C-2-SYMMETRICAL DISULFONAMIDE AS A CHIRAL LIGAND - SIMMONS-SMITH CYCLOPROPANATION OF ALLYLIC ALCOHOLS BY THE ET(2)ZN-CH2I2-DISULFONAMIDE SYSTEM
    TAKAHASHI, H
    YOSHIOKA, M
    SHIBASAKI, M
    OHNO, M
    IMAI, N
    KOBAYASHI, S
    TETRAHEDRON, 1995, 51 (44) : 12013 - 12026
  • [8] A new chiral disulfonamide ligand derived from alpha-amino acid for catalytic enantioselective cyclopropanation
    Imai, N
    Sakamoto, K
    Maeda, M
    Kouge, K
    Yoshizane, K
    Nokami, J
    TETRAHEDRON LETTERS, 1997, 38 (08) : 1423 - 1426
  • [9] Catalytic allylic oxidation with a recyclable, fluorous seleninic acid
    Crich, D
    Zou, YK
    ORGANIC LETTERS, 2004, 6 (05) : 775 - 777
  • [10] Catalytic enantioselective bromoamination of allylic alcohols
    Qi, Juan
    Fan, Guo-Tao
    Chen, Jie
    Sun, Ming-Hui
    Dong, Yu-Ting
    Zhou, Ling
    CHEMICAL COMMUNICATIONS, 2014, 50 (89) : 13841 - 13844